Bench‐Stable α‐Fluoroamines: Synthesis, Properties, and Application in Medicinal Chemistry

Vadym Levterov; Oleh Shablykin; Oleksandr Stashkevych; Volodymyr Kokhalskyi; Vadym Konashuk; Iryna Sadkova; Olha Shevchuk; Petro Borysko; Henry S. Rzepa; Pavel K. Mykhailiuk

doi:10.1002/anie.5080799

Enriched recordOpen access

Bench‐Stable α‐Fluoroamines: Synthesis, Properties, and Application in Medicinal Chemistry

Vadym Levterov, Oleh Shablykin, Oleksandr Stashkevych, Volodymyr Kokhalskyi, Vadym Konashuk, Iryna Sadkova, Olha Shevchuk, Petro Borysko, Henry S. Rzepa, Pavel K. Mykhailiuk

Angewandte Chemie International Edition2026doi:10.1002/anie.5080799

Citation graph

Abstract

ABSTRACT Aliphatic N ‐unprotected α‐fluoroamines are unstable due to dehydrofluorination. Here, we show that the incorporation of the CH 2 ‐group into the elusive α‐fluoropiperidine provides a stable α‐fluoroamine with the 2‐azabicyclo[2.2.1]heptane core. The latter does not eliminate HF because of Bredt's rule. The high stability of this α‐fluoroamine allows its wide chemical modifications and use in medicinal chemistry.

Authors

Vadym Levterov#1 Oleh Shablykin#2 Oleksandr Stashkevych#3 Volodymyr Kokhalskyi#4 Vadym Konashuk#5 Iryna Sadkova#6 Olha Shevchuk#7 Petro Borysko#8 Henry S. Rzepa#9 Pavel K. Mykhailiuk

Referenced works

View all references →

No local reference links have been materialized yet.

Cited by

View all cited-by records →

No local citing links have been materialized yet.

External reference records

10.1021/jm4017625

10.1021/acs.jmedchem.2c00473

10.1002/anie.201703801

10.1002/anie.202311583

10.1002/anie.202304246

10.1002/anie.202418850

10.1002/anie.202517814

10.1021/jo00913a900

10.1021/jo01319a023

10.1038/s41557‐018‐0197‐2

10.1021/acscatal.0c03278

10.1021/jm981133m

Bench‐Stable α‐Fluoroamines: Synthesis, Properties, and Application in Medicinal Chemistry

Referenced works

Cited by

External reference records

Additional external references